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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Francisco Encarnación# | .698 | 2051-2059 | |
| 2 | Rafael González | .637 | 2033-2039 | |
| 3 | Ricardo Fraga | .616 | 2030-2037 | |
| 4 | Joaquín Pérez | .594 | 2033-2037 | |
| 5 | Vincent Sturm# | .587 | 2051-2059 | |
| 6 | Fernando Reyna | .582 | 2015-2027 | |
| 7 | Miguel Mora | .566 | 2015-2020 | |
| 8 | Raúl Pérez | .560 | 2015-2028 | |
| 9 | Teddy Barnes | .552 | 2049-2052 | |
| 10 | Gerard Fyson | .551 | 2040-2045 | |
| 11 | José Santiago | .532 | 2028-2032 | |
| 12 | Romano Martínez | .493 | 2024-2029 | |
| 13 | Il-gyung Kim | .453 | 2017-2026 | |
| 14 | Mark Brunswick | .442 | 2042-2048 | |
| 15 | Xavier Padilla | .439 | 2025-2031 |
